Abstract
cis-5-Phenyl prolinates with electrophilic substituents at the fourth position of a pyrrolidine ring were synthesized by 1,3-dipolar cycloaddition of arylimino esters with divinyl sulfone and acrylonitrile. 4-Vinylsulfonyl 5-phenyl prolinates inhibit Staphylococcus aureus sortase SrtA irreversibly by modification of the enzyme Cys184 and could be used as hits for the development of antibacterials and antivirulence agents.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Aminoacyltransferases / antagonists & inhibitors*
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Aminoacyltransferases / metabolism
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Anti-Bacterial Agents / chemical synthesis*
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / pharmacology
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Bacterial Proteins / antagonists & inhibitors*
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Bacterial Proteins / metabolism
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Cysteine Endopeptidases / metabolism
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology
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Proline / analogs & derivatives*
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Proline / chemistry
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Protein Isoforms / antagonists & inhibitors
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Protein Isoforms / metabolism
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Staphylococcus aureus / enzymology*
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Sulfones / chemical synthesis*
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Sulfones / chemistry
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Sulfones / pharmacology
Substances
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5-phenyl proline
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Anti-Bacterial Agents
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Bacterial Proteins
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Enzyme Inhibitors
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Protein Isoforms
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Sulfones
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divinyl sulfone
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Proline
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Aminoacyltransferases
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sortase A
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Cysteine Endopeptidases